Classifications

• • C—CHEMISTRY; METALLURGY
  • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
  • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
  • C10M111/00—Lubrication compositions characterised by the base-material being a mixture of two or more compounds covered by more than one of the main groups C10M101/00 - C10M109/00, each of these compounds being essential
  • C10M111/04—Lubrication compositions characterised by the base-material being a mixture of two or more compounds covered by more than one of the main groups C10M101/00 - C10M109/00, each of these compounds being essential at least one of them being a macromolecular organic compound
• • C—CHEMISTRY; METALLURGY
  • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
  • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
  • C10M105/00—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound
  • C10M105/08—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound containing oxygen
  • C10M105/18—Ethers, e.g. epoxides
• • C—CHEMISTRY; METALLURGY
  • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
  • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
  • C10M107/00—Lubricating compositions characterised by the base-material being a macromolecular compound
  • C10M107/02—Hydrocarbon polymers; Hydrocarbon polymers modified by oxidation
  • C10M107/10—Hydrocarbon polymers; Hydrocarbon polymers modified by oxidation containing aliphatic monomer having more than 4 carbon atoms
• • C—CHEMISTRY; METALLURGY
  • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
  • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
  • C10M2203/00—Organic non-macromolecular hydrocarbon compounds and hydrocarbon fractions as ingredients in lubricant compositions
  • C10M2203/06—Well-defined aromatic compounds
• • C—CHEMISTRY; METALLURGY
  • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
  • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
  • C10M2205/00—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions
  • C10M2205/02—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions containing acyclic monomers
  • C10M2205/028—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions containing acyclic monomers containing aliphatic monomers having more than four carbon atoms
• • C—CHEMISTRY; METALLURGY
  • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
  • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
  • C10M2205/00—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions
  • C10M2205/02—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions containing acyclic monomers
  • C10M2205/028—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions containing acyclic monomers containing aliphatic monomers having more than four carbon atoms
  • C10M2205/0285—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions containing acyclic monomers containing aliphatic monomers having more than four carbon atoms used as base material
• • C—CHEMISTRY; METALLURGY
  • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
  • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
  • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
  • C10M2207/04—Ethers; Acetals; Ortho-esters; Ortho-carbonates
• • C—CHEMISTRY; METALLURGY
  • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
  • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
  • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
  • C10M2207/04—Ethers; Acetals; Ortho-esters; Ortho-carbonates
  • C10M2207/0406—Ethers; Acetals; Ortho-esters; Ortho-carbonates used as base material

Definitions

• the invention relates to synthetic lubricant base stocks, and more particularly to synthetic lubricant base stocks having a good viscosity. Some of these also exhibit a low pour point.
• Synthetic lubricants prepared from man-made base stocks have uniform molecular structures and, therefore, well-defined properties that can be tailored to specific applications.
• Mineral oil base stocks are prepared from crude oil and are complex mixtures of naturally occurring hydrocarbons. The greater uniformity of synthetic lubricants generally results in superior performance properties.
• synthetic lubricants have excellent thermal stability. As automobile engines are reduced in size to save weight and fuel, they run at higher temperatures, and therefore require a more thermally stable oil. Because lubricants made from synthetic base stocks have such properties as excellent oxidative/thermal stability, very low volatility, and good viscosity indices over a wide range of temperatures, they offer better lubrication and permit longer drain intervals, with less oil vaporization loss between oil changes.
• Synthetic base stocks may be prepared by oligomerizing internal and alpha-olefin monomers to form a mixture of dimers, trimers, tetramers, and pentamers, with minimal amounts of higher oligomers. The unsaturated oligomer products are then hydrogenated to improve their oxidative stability, with little change in other properties. The resulting synthetic base stocks have uniform isoparaffinic hydrocarbon structures, similar to those of high quality paraffinic mineral base stocks, but have the superior properties mentioned because of their greater uniformity.
• Synthetic base stocks are produced in a broad range of viscosity grades. It is common practice to classify the base stocks by their viscosities, measured in centistokes (cSt) at 100°C. Those base stocks with viscosities less than or equal to 4 cSt are commonly referred to as “low viscosity” base stocks, whereas base stocks having a viscosity of 40 to 100 cSt are commonly referred to as “high viscosity” base stocks. Base stocks having a viscosity of 4 to 8 cSt are referred to as “medium viscosity" base stocks. The low viscosity base stocks generally are recommended for low temperature applications.
• Base stocks for higher temperature applications such as motor oils, automatic transmission fluids, turbine lubricants, and other industrial lubricants, generally require higher viscosities, such as those provided by medium viscosity base stocks (i.e. 4 to 8 cSt grades).
• medium viscosity base stocks i.e. 4 to 8 cSt grades.
• High viscosity base stocks are used in gear oils and as blending stocks.
• the viscosity of the base stocks generally is determined by the length of the oligomer molecules formed during the oligomerization reaction. The degree of oligomerization is affected by the catalyst and reaction conditions employed during the oligomerization reaction. The length of the carbon chain of the monomer starting material also has a direct influence on the properties of the oligomer products. Fluids prepared from short-chain monomers tend to have low pour points and moderately low viscosity indices, whereas fluids prepared from long-chain monomers tend to have moderately low pour points and higher viscosity indices. Oligomers prepared from long-chain monomers are generally more suitable for use as medium viscosity synthetic lubricant base stocks than those prepared from shorter-chain monomers.
• oligomerizing long-chain olefins to prepare synthetic lubricant base stocks is to contact the olefin with boron trifluoride, together with a promoter, at a reaction temperature sufficient to effect oligomerization of the olefin, as described in US-A-4400565, -4420646, -4420647 and -4434308.
• Boron trifluoride gas (BF 3 ) is however a pulmonary irritant, and breathing the gas, or fumes formed by hydration of the gas with atmospheric moisture, poses hazards preferably avoided. Additionally, the disposal/neutralization of BF 3 raises environmental concerns.
• a method for oligomerizing long-chain olefins using a non-hazardous, non-polluting catalyst would be a substantial improvement in the art.
• the viscosity (and in some instances the pour point) of base stocks prepared in this manner may be improved by co-reacting a major amount of long-chain linear olefin and minor amount of certain aromatic compounds (i.e. in a mole ratio of about 3:1 or greater), for example anisole, diphenyl ether and/or diphenyl.
• a major amount of long-chain linear olefin and minor amount of certain aromatic compounds i.e. in a mole ratio of about 3:1 or greater
• anisole, diphenyl ether and/or diphenyl for example anisole, diphenyl ether and/or diphenyl.
• the resulting mixtures of oligomers and alkylated anisoles, phenyl ethers and/or alkylated diphenyls exhibit a good viscosity and, with the alkylated diphenyl ethers and a diphenyls, a pour point substantially lower than that observed in base stocks comprising the olef
• oligomers and alkylated anisoles, alkylated diphenyl ethers and/or alkylated diphenyls may be hydrogenated (to alkanes and alkylated cyclohexyl ethers and/or alkylated dicyclohexanes) to enhance their oxidative stability.
• US-A-4480142 discloses a process for preparing alkylated polycyclic aromatics by contacting the aromatic compound with an alpha olefin in a mole ratio of olefin to aromatic of up to 2.5:1. An acidic montmorillonite clay is used to catalyze the reaction.
• One embodiment of this invention provides a synthetic lubricant base stock comprising oligomers prepared from an olefin composition comprising a linear olefin having from 10 to 24 carbon atoms, which base stock additionally contains an alkyl-substituted diphenyl, diphenyl ether or anisole having the formula: wherein R 1 is a group of the formula and where R 2 , R 3 , R 4 , R 5 , R 6 and R 7 are each H or an alkyl group having 1 to 24 carbon atoms, provided that at least one of R 2 , R 3 , R 4 , R 5 , R 6 and R 7 is an alkyl group containing from 10 to 24 carbon atoms, R11 is an alkyl group having 1 to 10 carbon atoms; R 2 is an alkyl group having 10 to 24 carbon atoms; and R 3 and R 4 are each H or an alkyl group having up to 10 carbon atoms.
• An embodiment of this invention provides such a composition which additionally contains an alkyl-substituted aromatic or cycloaliphatic compound having the formula: and where R 2 to R 7 and R 11 to R 14 have the meanings given above.
• the linear olefins can comprise alpha-olefins, internal olefins or a mixture thereof.
• the olefin composition comprises said linear olefins and up to 20 weight % of propylene or of 1,3-diisopropenyl benzene or alpha-methyl styrene.
• the olefin composition can comprise said linear olefins and a vinylidene olefin having 10 to 24 carbon atoms, e.g. 5 to 40 weight % of the vinylidene olefin.
• the invention also provides a process for producing a synthetic lubricant base stock as defined above by contacting the olefin composition with an acidic montmorillonite clay in the presence of an alkyl-substituted diphenyl, diphenyl ether or anisole having the formula wherein R 1 is a group of the formula where R 2 to R 7 have the meanings given above provided at least one of R 2 to R 7 is hydrogen, R11 is alkyl having 1 to 10 carbon atoms, R 12 is hydrogen, and R 13 and R 14 are each hydrogen or alkyl ethers and/or alkylated diphenyls contained in the mixture may then be hydrogenated, to obtain a mixture of reduced oligomers and alkylated cyclohexyl ethers and/or alkylated dicyclohexanes.
• the resulting base stocks contain from 1 to 50 wt.% of alkylated cyclohexyl ethers and/or alkylated dicyclohexanes. More preferably, the resulting base stocks contain from 5 to 25 wt.% of alkylated cyclohexyl ethers and/or alkylated diclohexanes.
• one skilled in the art may use those hydrogenation conditions which will reduce only the oligomers, to obtain a mixture comprising reduced oligomers and alkylated phenyl ethers and/or alkylated diphenyls.
• One skilled in the art also may find it desirable to use those hydrogenation conditions which will reduce the oligomers and a portion of the alkylated phenyl ethers and/or alkylated diphenyls, to obtain a mixture comprising reduced oligomers, alkylated phenyl ethers and/or alkylated diphenyls and alkylated cyclohexyl ethers and/or alkylated dicyclohexanes.
• Compounds with one aromatic ring and one cyclohexyl (reduced) ring may be prepared and included as well.
• the viscosity of the base stocks is improved when the starting materials comprise a mixture of long-chain linear olefin and anisole, preferably from 1 to 40 wt.% of anisole (i.e. a weight ratio of anisole to linear olefin of 1:99 to 2:3). More preferably, the mixture of long-chain linear olefin and anisole contains from 5 to 25 wt.% of anisole (i.e. a weight ratio of anisole to linear olefin of 1:20 to 1:4). It is especially preferred that the mixture of long-chain linear olefin and anisole contain about 20 wt.% anisole (i.e.
• the resulting base stocks contain from 1 to 80 wt.% alkylated methoxycyclohexane. More preferably, the resulting base stocks contain from 5 to 40 wt.% of alkylated methoxycyclohexane. having 1 to 10 carbon atoms.
• the clay can optionally be activated with a Lewis acid.
• the alkylation-oligomerization product of this reaction can be completely or partially hydrogenated.
• phenyl ether and/or diphenyl indicates that the mixture may contain one of the following: (1) phenyl ether and no diphenyl; (2) diphenyl and no phenyl ether; or (3) both phenyl ether and diphenyl in a ratio of phenyl ether to diphenyl of 1:99 to 99:1.
• the use of "and/or” in connection with other components of mixtures described herein is to be interpreted similarly, indicating the presence of either (or, if three or more, any) component without the other(s), or both (or, if three or more, some or all).
• the starting material used to prepare the base stocks of the present invention comprise a mixture containing a long-chain linear olefin and certain aromatic compounds in a mole ratio of olefin to aromatic compound of 3:1 or greater.
• Co-reacting a major amount of linear olefin feed with a minor amount of anisole, phenyl ether and/or diphenyl produces a mixture of olefin oligomers with alkylated anisoles, alkylated phenyl ethers and/or alkylated diphenyls.
• the resulting base stocks contain from 1 to 50 wt. % of alkylated phenyl ethers and/or alkylated diphenyls.
• the resulting base stocks contain from 5 to 25 wt.% of alkylated phenyl ethers and/or alkylated diphenyls.
• the double bonds present in the oligomers and alkylated phenyl may find it desirable to use those hydrogenation conditions which will reduce only the oligomers, to obtain a mixture comprising reduced oligomers and alkylated anisoles.
• One skilled in the art also may find it desirable to use hydrogenation conditions which will reduce the oligomers and a portion of the alkylated anisoles, to obtain a mixture comprising reduced oligomers, alkylated anisoles and alkylated methoxycyclohexanes.
• a preferred range for the total number of carbon atoms in any one olefin molecule is 12 to 18, inclusive, with any especially preferred range being 13 to 16, inclusive.
• Anisole also known as methyl phenyl ether, may be obtained by processes well-known to those skilled in the art and is commercially available. While anisole is preferred in this embodiment of the present invention, acceptable substitutes for anisole include those compounds having the following structure: where R11 is an alkyl group having 1 to 10 carbon atoms; R 12 is hydrogen. and R 13 amd R14 are each hydrogen or an alkyl group having 1 to 10 carbon atoms.
• Diphenyl ether and diphenyl may be obtained by processes well-known to those skilled in the art and are commercially available. While diphenyl ether (C 6 H 5 OC 6 H 5 ) and diphenyl (C 6 H 5 C 6 H 5 ) are preferred in this embodiment of the present invention, acceptable substitutes for diphenyl ether and diphenyl include those aromatic compounds having the following structures: and where R 2 , R 3 , R 4 , R 5 , R 6 , and R 7 are each hydrogen or an alkyl group having from 1 to 24 carbon atoms. It is preferred that R 2 , R 3 , R 4 , R 5 , R 6 , and R 7 contain no more than 10 carbon atoms. At least one of R2, R3, R4, R 5, R 6 , or R 7 is H.
• Oligomerization of linear olefins may be represented by the following general equation: where n represents moles of monomer and m represents the number of carbon atoms in the monomer.
• oligomerization of 1-decene may be represented as follows:
• olefin monomer reacts with olefin monomer to form dimers.
• dimers that are formed then react with additional olefin monomer to form trimers, and so on.
• m the number of carbon atoms in the olefin monomer.
• poly-alkylation of the phenyl ether anisole and/or diphenyl also will occur.
• the alkylation of phenyl ether, anisole and/or diphenyl by linear olefin feed occurs concurrently with the oligomerization of the olefin feed.
• the co-reaction results in a mixture of oligomers (dimers, trimers, tetramers, etc) and alkylated phenyl ether, alkylated anisole, and/or alkylated diphenyls, including mono-, di-, and tri- alkylated phenyl ether -anisole, and/or -diphenyl.
• the number of carbon atoms in the alkyl groups of the alkylated phenyl ether, anisole, and/or alkylated diphenyls will correspond to the number of carbon atoms in the linear olefin feed.
• the alkyl groups of the alkylated phenyl ether, anisole, and/or alkylated diphenyls will have from 10 to 24 carbon atoms.
• silica-alumina clays also called aluminosilicates.
• Silica-alumina clays primarily are composed of silicon, aluminium and oxygen, with minor amounts of magnesium and iron in some instances. Variations in the ratios of these constituents, and in their crystal lattice configurations, result in some fifty separate clays, each with its own characteristic properties.
• silica-alumina clays comprises smectite clays, which have a small particle size and unusual intercalation properties which afford them a high surface area.
• Smectites comprise layered sheets of octahedral sites between sheets of tetrahedral sites, where the distance between the layers can be adjusted by swelling, using an appropriate solvent.
• Three-layered sheet-type smectites include montmorillonites.
• the montmorillonites structure may be represented by the following formula where M represents the intermellar (balancing) cations, normally sodium or lithium; and x, y and n are numbers.
• Montmorillonite clays may be acid-activated by such mineral acids as sulphuric acid and hydrochloric acid. Mineral acids activate montmorillonites by attacking and solubilizing structural cations in the octahedral layers. This opens up the clay structure and increases surface area. These acid-treated clays act as strong Bronsted acids. We have discovered that certain acid-treated montmorillonite clay catalysts are particularly effective for preparing synthetic lubricant base stocks in good yield by oligomerizing long-chain olefins.
• These clays are acidic calcium montmorillonite clays having a moisture content of up to 20 wt.%, a residual acidity of 3 to 30mg KOH/g (when titrated to a phenolphthalein end point), and a surface area of 300 M 2 /g or more.
• Illustrative examples include Filtrol grade 24, having a moisture content of 12 wt.%, a residual acidity of 8.5 mg KOH/g and a surface area of 425 M 2 /g; Filtrol grade 124, having a moisture content of 2 wt%, residual acidity of 7.0 mg KOH/g, and a surface area of 400 M 2 /g; Filtrol grade 13, having a moisture content of 16 wt.%, a residual acidity of 15 mg KOH/g, and a surface area of 300 M 2 /g; Filtrol grade 113, having a moisture content of 4 wt.%, a residual acidity of 10 mg KOH/g, and a surface area of 300 M 2 /g; and Filtrol grade 224, having virtually no moisture, and having a residual acidity of 3.0 mg KOH/g, and a surface area of 350 M 2 /g.
• the clay catalyst is activated by heat treatment before running the co-reactions.
• heat treatment of the catalyst before running an oligomerization reaction causes the catalyst to be more active and to produce a higher olefin conversion.
• clays heat treated in this manner are more stable, remaining active for a long period during a reaction.
• the clays may be heat treated at temperatures of 50 to 400 C, with or without the use of a vacuum. A more preferred temperature range is 50 to 300 C.
• an inert gas may be used during heat treatment as well.
• the clay should be heat treated under conditions and for a length of time which will reduce the water content of the clay to approximately 1 wt.% or less.
• the clay may also be activated by a Lewis acid, see our prior Application (P23492) 91302130.9.
• the oligomerization and alkylation co-reactions may be carried out in a stirred slurry reactor or in a fixed bed continuous flow reactor.
• the catalyst concentration should be sufficient to provide the desired catalytic effect.
• the temperatures at which the oligomerization and alkylation may be performed are generally from 50 to 300 C, with the preferred range being from 150 to 180°C.
• the reactions may be run at pressures of from 0.1 to 7 MPa (0 to 1000 psig).
• the partially unsaturated oligomers are completely reduced via catalytic hydrogenation.
• the alkylated phenyl ethers, alkylated anisoles, and/or alkylated diphenyls may be completely or partially reduced as well, or, if desired, may remain in the aromatic form; preferably, they are completely reduced.
• Hydrogenation of the oligomers and the alkylated anisole, alkylated phenyl ether and/or alkylated diphenyls improves their thermal stability and helps prevent oxidative degradation during use of the mixture as a lubricant.
• the hydrogenation reaction for 1-decene oligomers may be represented as follows: where n represents moles of monomer used to form the oligomer.
• the complete hydrogenation of a mono-alkylated phenyl ether, mono-alkylated anisole, or mono-alkylated diphenyl may be represented respectively, as follows:
• a number of metal catalysts are suitable for promoting the hydrogenation reaction, including nickel, platinum, palladium, copper, and Raney nickel. These metals may be supported on a variety of porous materials, such as kieselguhr, alumina, or charcoal.
• a particularly preferred catalyst for this hydrogenation is a nickel-copper-chromia catalyst described in US-A-3152998 other known hydrogenation procedures are disclosed in US-A-4045508, -4013736, -3997621 and -3997622.
• the hydrogenation conditions described in the examples below may be employed.
• less vigorous conditions such as the following: using a 0.5% palladium on alumina catalyst (10 wt.% based on charge), pressurize to 3.5 MPa (500 psig) with hydrogen and heat to 90 C; re-pressurize to 7MPa (1000 psig) with hydrogen as needed, for 4 hours.
• Unreacted monomer and anisole, phenyl ether and/or diphenyl may be removed either before or after hydrogenation
• unreacted monomer and anisole, phenyl ether and/or diphenyl may be stripped from the oligomers/alkylated phenyl ethers, alkylated anisoles, and/or alkylated diphenyls before hydrogenation and recycled to the catalyst bed for co-reaction.
• the removal or recycle of unreacted monomer and anisole, phenyl ether and/or diphenyl or, if after hydrogenation, the removal of non-oligomerized alkane and non-alkylated cyclohexyl ethers and/or non-alkylated dicyclohexanes, should be conducted under mild conditions using vacuum distillation procedures known to those skilled in the art. Distillation at temperatures exceeding 250 C may cause the oligomers to break down in some fashion and come off as volatiles. Preferably, therefore, the reboiler or pot temperature should be kept at or below 255 C most preferably at or below 180C. Procedures known by those skilled in the art to be alternatives to vacuum distillation also may be employed to separate unreacted components from the mixture.
• Reactants and clay catalyst were charged to a three-necked flask equipped with an overhead stirrer, heating mantle, and a nitrogen purge. The mixture was vigorously stirred and heated at the desired temperature for the desired period of time. At the end of the reaction, the mixture was cooled to ambient temperature and filtered with suction. Percentage olefin conversion and dimer/trimer ratio were determined by liquid chromatography and recorded in the Tables below.

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• 1991
  • 1991-05-14 EP EP91304307A patent/EP0466307A1/fr not_active Ceased
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